


an angel with black wings will finally prove that this is love

by potsu



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Crossdressing, Cunnilingus, F/M, Female Ejaculation, First Time, M/M, Misgendering, Plot What Plot/Porn Without Plot, Trans Female Character, Vaginal Fingering, Vaginal Sex, Verbal Humiliation, but no misgendering of the transgender character, some non-negotiated kink
Language: English
Status: In-Progress
Published: 2014-03-27
Updated: 2014-03-27
Packaged: 2018-01-16 22:41:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,160
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1364410
Author URL: https://archiveofourown.org/users/potsu/pseuds/potsu
Summary: <blockquote class="userstuff">
              <p>alternate titles</p><p>"The Gradual Queering of Dean Winchester"</p><p>or</p><p>"Four Times Dean Fucked a Woman, and One Time a Non-Gendered Angel in the Body of a Cis Male Fucked Dean"</p><p>or</p><p>"How I learned to Quit Worrying and Love Angelic Dickings"</p>
            </blockquote>





	1. Ofelia

**Author's Note:**

> official title comes from "Humanitarianism" by Zeigeist
> 
> "A million of worse things  
> Worse than kissing you  
> An angel with black wings  
> Will finally prove  
> That this is love"
> 
> alternate titles were to amuse myself, but are also accurate
> 
> the opinions about sex and gender expressed in this fic are not necessarily those of the author; rather, they're the author's opinions about Dean's opinions
> 
> some tags apply to later chapters

**Summary for the Chapter:**

> I may have described an actual bar that actually exists.
> 
> Take note, I prefer to use the word "cunt" when referring to genitals and will do so unless I think that a certain character would use a different term.

It was an old house that had been converted into a bar, and it was nicer than most of the bars that Dean went to. It had a bunch of hipster beers with weird names, but they tasted good enough and they weren't too expensive. There was a massive back yard with tables and benches and Christmas lights hanging everywhere. College kids and professor-types rubbed elbows as they drank, smoked, scribbled on papers, or clacked away on laptops. Dogs ran between the tables and delivery men from nearby restaurants wandered up to the fence to hand over pizzas or sandwiches. It was the perfect place to sit in the darkening evening, people-watching, eavesdropping, and trying not to die in the fucking Texas heat.

Dean was finishing off beer number three, doing his best not to understand how college-life had appealed to Sammy, when a loud, hoarse laugh cut across the noise of the yard. The laugh belonged to a woman with long black hair. Her skin was the color of the red-brown earth that Dean had seen in deserts and the Grand Canyon, and there were tattoos of bright flowers on her shoulders. She tried to drink from her pint glass but she was laughing too hard and the glass bumped her mouth, sloshing beer onto the ground, and she just laughed harder. She stood up, ostensibly to replace her spilled drink, and Dean got a good look at her.

She was... well, _fat_. Not curvy, just _fat_. But she didn't dress like any of the fat girls Dean had seen before; she didn't try to hide her shape or weight. A red halter top showed off the rolls of flesh on her back and the size of her upper arms; some of her belly even hung out from under it. Her ragged jean shorts tucked under that exposed belly and pressed into the brown flesh of her thighs. To his surprise, Dean found himself noticing how her fleshy arms made her small hands look even more delicate, how her cheeks dimpled every time she laughed, how her upper lip was exactly the shape of an 'm', and that her strappy sandals made her cankles look cute. Mostly, Dean noticed how _happy_ she looked, laughing and wiping at the beer that had spilled on her shirt. Dean's dick had rarely lead him wrong, so he followed it's suggestion and sauntered up to her before she made it back inside to the bar.

"Hey, let me get your next drink."

She smiled and her round cheeks dimpled.

"Thanks! I'm Ofelia. I ain't seen you before; it's not a big town, so you gotta be new."

Her voice was scratchy with a Texas drawl to it, lazy and slow.

"I'm Dean. I'm just passing through and thought this looked like a nice place for a drink. Didn't think I'd find anything else, but then I saw you."

Ofelia's dimples deepened.

 

 

* * *

 

 

Ofelia lived in an old house with creaky wooden floors, not too different from the house that had been turned into a bar. She held Dean by both hands and walked backwards to her room, pausing occasionally to kiss him. She smiled after each kiss.

"All my roommates are out of town or stayin' somewhere else tonight, so we don't gotta worry about bein' quiet."

"Oh?" said Dean, "Are you gonna get noisy for me?"

Ofelia laughed heartily, head thrown back, brown throat exposed.

"Oh, _honey_ , I'm always noisy! If the neighbors' dogs ain't howlin' by the time I cum, then you're shit in bed."

Dean had to laugh too, her laughter was so infectious. "I'll take that challenge. I'll get you to drown out the dogs!"

Her bedroom was sparsely furnished -- just a desk with a laptop, a rolling chair, and a large mattress on the floor. The rest of the free space was taken up by canvases and bottles of paint. An art student, Dean figured. Ofelia sat down heavily on the mattress and tugged Dean down so that he straddled her thick thighs. She didn't even undo the ties of her halter top, just yanked it up over her head so that her breasts and stomach were bared. Her breasts were large, with wide brown nipples and her navel was a dark indentation in the rolls of her belly. Dean had been with some busty girls before, but none of them had been as well-endowed as Ofelia. He went to cup her breasts but they were so large that, even with his fingers and thumbs spread out, his hands vanished beneath them. Dean couldn't stop from grinning as he hefted their soft weight in his hands. Ofelia laughed and placed her hands over his, causing him to clutch tighter at her breasts. Dean hunched forward to lick at a nipple and she began to push his overshirt back from his shoulders. God, her nipples were so _big_ , he had to open his mouth wide to suck the whole of one.

Ofelia pushed him away and his mouth came off her nipple with an audible _slurp_. She laughed again, pulled his t-shirt up over his head, and tossed it somewhere onto the floor. Smiling, she reached for him, and pulled him into a hug. It was strange, a reversal of how things usually went, to sit in her lap and be held. But Dean didn't feel uncomfortable, on the contrary, he felt _very_ comfortable. Ofelia cradled him, big arms pressed around his sides, big breasts pressed against his chest, big belly pressed against his groin. They kissed like that for awhile, warm and sloppy, until Dean drew back.

"Want me to go down on you?" he asked.

Ofelia's smile was so big that her eyes scrunched up. "Like you hafta ask? Dean, honey, knock yourself out!"

She lay back and pushed her shorts off, lifting up her hips to get them down her ample butt and thighs. When the shorts were down to her pudgy ankles, she kicked them off.

Truth be told, Dean loved going down on ladies just as much as he loved fucking them. He loved their hands in his hair, their taste in his mouth, their smell in his nostrils, the feel of their flesh under his tongue. Hell, even picking the occasional pubic hair out of his teeth wasn't too bad, it was just a reminder of what he'd gotten up to the night before. Going down on Ofelia felt especially intimate, because he had to push her belly up to get to the rosy flesh of her cunt. Dean was cuddled between her thighs and under her belly, aware only of girl-skin and girl-taste, like he was in the world's best pillow fort. Which was a weird, not very sexy thought, but totally awesome in practice.

Dean started out slow, licking along Ofelia's labia, but her raspy voice instructed him to "Suck me! C'mon, suck me, honey!"

Dean got his lips around her clit, teeth very carefully pushing back the clitoral hood, and began with short, pulsing sucks at her clit. Ofelia moaned and reached down to hold her belly up so that Dean's hands were free. He got his left shoulder under her ass, wrapped his arm around her thigh, and lifted her up a little so that he could get the fingers of his right hand into her cunt-hole. He stroked his fingers in and out, bumping against his own chin as he continued to suck at her. Ofelia was getting louder, so Dean sped up. He was panting through his nose and he could feel her thighs and stomach begin to tremble. Her voice went _very_ loud then, hoarse "Ah! Ah! Ah!"s and Dean drew on her clit in long, hard sucks. Her whole body jolted at each suck and her heel thumped against his back. Ofelia's "Ah!"s turned into laughter and Dean drew away from between her legs.

She lay, legs still spread open, belly wobbling as she laughed.

"Aw, Dean, that was _nice_. See? The dogs are barkin'!"

Sure enough, some dog was yapping outside.

Ofelia's laughter trailed off into a huge, contented sigh. She smiled and dimpled at him and Dean was suddenly aware that he was _very_ hard.

"Do you mind if I...?" Dean gestured to the front of his jeans.

"Get those off! I'll grab a condom and we'll see about drownin' out that dog."

Dean kicked off his jeans and underwear, just as uncaring of where they landed as Ofelia had been with the rest of their clothes. Ofelia retrieved a condom from the desk drawer and was kneeling on the mattress by the time Dean had finished stripping. She eyed his cock appreciatively as she opened the condom wrapper.

"That's a mighty fine piece, honey. Might put some of my toys to shame."

She rolled the condom onto him, quick and efficient, and lay back again, holding open her legs with hands on the insides of her thighs.

"C'mon. I wanna see if you can work your dick as good as your tongue."

Dean smiled as he settled between her thighs, "Can't have you thinking I'm shit in bed."

"You're about halfway to provin' that you ain't shit in bed."

Dean got a hand around his dick and pressed the tip of it into Ofelia's cunt. "I don't like leaving jobs half done..."

She laughed, smacked her hands down onto Dean's ass, and yanked him all the way into her.

Dean kissed down her neck and sucked at her wide nipples. He rocked into her, hipbones pushing into the softness of her hips, and Ofelia's moans bubbled with laughter. Dean fucked her faster and she just laughed louder and hooked her thick ankles around his lower back. Fucking Ofelia was being enveloped by her. Her hot wet cunt around his dick, sweaty thighs and arms holding him, belly and breasts soft against him. She was everything Dean loved about women, but _amplified_. She made him feel desperate and overwhelmed. Dean shoved his face into the crook of her shoulder and breathed in the smell of her sweat. His grunts of pleasure and the yapping of the dog were lost under the sound of Ofelia's laughter. Dean was fucking into her _hard_ , this was supposed to be about _his_ power and skill in bed, but she just absorbed it all and enjoyed it all; Dean wasn't sure if he wanted her to surrender to him, to say that his dick was too big, his thrusts too hard, or if he wanted to surrender to her, to fuck himself sore, jizz himself empty into the lushness of her body. In the end, it didn't matter what Dean wanted because she took the strength of his thrusts and cradled him and clutched at him and laughed with so much _happiness_ and Dean surrendered.

Ofelia went quiet when Dean's hips stuttered. He made embarrassingly shocked-sounding gasps and hid his face against her neck.

Dean was used to women resting their heads on his chest after sex but, again, Ofelia reversed things. After disposing of the condom, she pulled Dean's head down to be pillowed on one of her large breasts. Dean flung an arm across her belly and Ofelia stroked the back of his neck. They lay like that for awhile, as their breathing gentled back to normal. Eventually, Ofelia broke the silence.

"I'm gonna sound like a total cliche, but that made me hungry. You ain't shit in bed, so I figure I might should feed you. I got leftover pizza and some pie, I think."

Dean smiled and hugged her tight for a moment.

"I _love_ pie."

 

 

* * *

 

 

Several months later, Dean was at another bar, not early as nice as the one in Texas, catching up with his Dad about their respective hunting trips. The night grew long and they were running out of stories to tell each other, getting dangerously close to talking about Sammy's absence, when Dean spotted a woman sitting alone at the bar. She was fat, with black hair in a crisp bob. Her black dress was tight, it clung to the rolls of her belly and stretched taught across her thighs. Her lipstick was dark red, so dark it almost matched her dress and her hair. Dean caught the attention of the bartender and told him to send the lady another of whatever she was drinking.

John raised his eyebrows at Dean.

"What?"

"Well, she doesn't look like your usual type."

Dean shrugged his shoulders. "No reason that I should deprive the ladies of the world my company just because of their size."

The bartender handed the woman a margarita and pointed in Dean's direction. She looked him up and down, took a sip of her margarita, and gestured that Dean should come join her.

Dean stood up from the table. "Don't wait up, Dad."

John just rolled his eyes and downed the rest of his beer.


	2. Zakiyyah

**Notes for the Chapter:**

> the technique described herein may not work for everybody when it comes to squirting
> 
> but it sure does work for me

The bar was dimly lit by fluorescent signs and smokey from cigarettes. Dean noticed her, sitting further down the bar, because of the way the neon lights reflected on her skin. Her skin was such a deep, dark brown that the light shone on it like the rainbows on an oil slick. Her hair was in short locs, kept back from her face by a red bandana. She saw Dean looking and she smiled, flashing pink gums and bright white teeth with a gap at the front.

Her tall red heels made her hips sway as she walked towards him. Dean didn't give a shit about what shoes a woman wore, but he was partial to the way they walked in heels -- dainty or predatory or sultry, he liked it all.

"My name's Zakiyyah," she said, as she laid her hand on Dean's arm. Her palm was chilly and damp from the beer bottle that she'd been holding.

Dean gave his most charming smile, the one that every girl liked, and looked up at her from under his eyelashes. "My name's not nearly as cool as yours. Just Dean."

She flashed her bright, gap-tooth smile again and said "Well, a boring name can be forgiven for somebody as handsome as you."

 

 

* * *

 

 

They were in his motel room and he was pulling her underwear down from beneath her skirt when she laid her hand on his forearm, just as she had in the bar. Dean looked up. Zakiyyah's face was twisted up with worry. "I oughta warn you," she said.

"What," said Dean as he continued to work her underwear down her thighs, "you got a funky birthmark or some crazy piercings? That don't bother me."

Zakiyyah laughed but still looked a bit concerned. "No, nothing like that. It's just... sometimes I squirt."

Dean stopped his determined progress. "Really? Never been with a lady that could do that. Why do you gotta warn me? Does it not feel good or something?"

Zakiyyah sat on the motel bed and pushed her underwear the rest of the way off before leaning forward to unbuckle her heels. "No! It feels great, I love it. It just freaks some guys out. And it can be a bit messy."

Dean crawled forward, sliding his body up against hers until they were laying back on the bed. He pushed his hands under her skirt and rubbed his thumbs into the hollows of her hipbones. "Mess don't bother me. Anyway, it's a motel bed; It's gonna get cleaned tomorrow. If it's something you like, I wanna do it for you."

Zakiyyah smiled and kissed him between the eyes. "Get back down where you came from and I'll tell you what to do."

Dean knelt on the floor, gripped Zakiyyah's hips and tugged her down so that her legs hung off the bed and her pelvis was in front of his face.

"C'mon, baby. Warm me up with your tongue."

"Yes, m'am!"

The flesh of Zakiyyah's thighs reflected the light of the bedside lamp in the same oil-slick manner that they had in the bar and the inner flesh of her cunt was as bright pink as her gums had been when she smiled. Dean licked big flat strokes along her labia, sucked the edges of them into his mouth, the way he'd sucked her tongue when they had kissed. Dean could hear her sighing and felt her hand come to rest on the top of his head. Zakiyyah didn't pull or push, just lightly pet his hair. Dean licked closer and closer to her clit, swirled his tongue over it, and licked at it from different directions, until he found that quick flicks of his tongue from the base of the clit caused Zakiyyah's thighs to shake. He kept at those little flicks and her sighing turned into groaning and his chin got wet from where it was pressed against the opening of her cunt. When Dean got his mouth around Zakiyyah's clit and _sucked_ , and her thighs went tight around his ears. She stayed tense like that for a moment and Dean gentled his sucking. She groaned loudly and the muscles in her thighs relaxed. Zakiyyah patted at Dean's hair until he moved away.

"You're real good at that." He could hear the smile in her voice, "Now, move back and get your fingers in me. Start slow. I'll take care up top."

She got her fingers into a v-shape, pointer and middle finger on either side of her clit. Dean got one finger into that hot wet opening, then two. He pushed his fingers in and out of her cunt slowly, while she worked her fingers up and down against her clit.

Dean was just about to go for a third finger when Zakiyyah said "Turn your hand palm up."

She made a small noise as Dean's fingers twisted inside her.

"Curl your fingers."

He did.

"Rock them forward. No, baby, no, don't push _in_ , push _up_."

Dean kept his fingers hooked and rocked his hand from the wrist, pushing up into the wall of her cunt. It wasn't his usual technique, but Zakiyyah seemed to enjoy it. She was groaning every time he rocked his fingers up, the flesh of her labia was darkening to red, and sweat was shining on her sides. Zakiyyah pressed down harder around her clit and rubbed faster.

"Harder, please. _Harder_."

Dean complied and he could see the muscles in her stomach tense.

"Fuck, baby, lean up here."

Dean got a knee up onto the bed and moved so that he was sitting to the side of her.

"Keep that hand working, baby. Now, put your other hand on me."

Dean hesitated, confused, until Zakiyyah patted the stretch of skin between her navel and her groin. There was a bit of maneuvering so that Dean could rest his hand there and she could twist her hand past his to continue rubbing her clit, but it wasn't so awkward as to ruin the mood.

"Just there, baby. Now, press down with the heel of your hand and press your fingers up. Hard."

Dean didn't want to hurt her, but, well, she did _ask_...

He rocked his hand up, felt the muscles in his forearm strain, and pressed down on her lower belly with the heel of his palm.

"Jesus Christ!" Dean couldn't help the shocked exclamation; he could _feel_ his fingers inside her, could feel the subtle shape under his palm as he pushed up into her.

"Just like that!" said Zakiyyah, from between clenched teeth.

Dean kept rocking his wrist up and blessed the years of monster hunting that had strengthened his arms. Zakiyyah was so wet around his fingers that he could hear it, sloppy and dirty-sexy. Dean pushed his fingers up and ground down with his palm and Zakiyyah shouted and her fingers slipped off her clit. Her arms went back to lever against the mattress and she arched her chest and belly to roll her pelvis down onto Dean's fingers. She shouted again and her cunt flexed around Dean's fingers, so forcefully that they were pushed out. He could see her cunt clench and then a dribble of fluid slipped between labia, puddled under her ass and darkened the bedsheets. Her hands grabbed at the sheets and her hips rolled against empty air. Dean stared.

"Oh god, put your fingers back in! Put 'em in!"

She sounded strained, gutted, like squirting was a Herculean task that took all her strength. Dean pushed his fingers back into her, just rubbing gently as she tensed around him. He felt a little spurt of fluid against the inside of his wrist. Nothing gross, just _warm,_ and _wet,_ and the smell of _sex,_ and Dean's dick blurted out pre-cum against his boxers. The way she moved, like she absolutely couldn't help it, the way her groans were deep and genuine -- Dean felt a stupid sense of pride that he helped her get to this point, that _he_ had done that and he wanted to _keep_ doing that.

Dean pressed his face in-between her thighs and got the flat of his tongue against that little twitching hole -- urethra, piss-hole -- not a hole he usually paid attention to or even associated with sex.

Well, not until _now_.

Zakiyyah made a strangled sound and kicked her heels back against the bed. Another spurt, right against his tongue, and Dean was pushing forward even more, trying to suck at that hole the way he'd sucked at her clit. His face was wet, from the bridge of his nose down, and his fingers had probably gone wrinkly from how slick she was. One more tiny squirt and now Zakiyyah _did_ grab his hair. She jerked his head back and held him away while she panted for breath. Dean was panting too, like he'd been deep-dicking her with all the strength of his back and thighs. Everything smelled like sex, and he was pretty sure that his dick was as wet as the sheets under Zakiyyah.

She let go of his hair and flopped back on the bed, completely relaxed.

"Get your pants open, get a condom on, and get your dick in me."

Dean didn't take his pants off, just unzipped and shoved them and his damp boxers below his ass; Zakiyyah was still in her clothes, even if her shirt was shoved up under her armpits and her skirt over her hips. He rolled the condom on and pressed into Zakiyyah.

Even through the condom, Dean could feel how wet and relaxed she was. She wound her arms around his neck and sighed. The intensity of fingering Zakiyyah until she squirted had ramped Dean up until he felt hot and jittery with arousal, so their fucking was almost excruciatingly gentle by contrast. His pace was lazy, as relaxed as she was, just rolling into her and feeling her cunt twitch around him, just sliding against Zakiyyah's slippery, over-sensitive flesh.

"You did so good, baby. You made me feel so good," she breathed into Dean's ear.

Her words brought back that ridiculous sense of pride and accomplishment. There were certain things that Dean _knew_ he was good at -- finding the best diner in any town, hunting monsters, fucking women -- but they weren't the sort of things that usually garnered praise. So to _hear_ it in Zakiyyah's warm, satisfied murmur, that did almost as much for Dean as fucking her did.

Zakiyyah tightened around him and sighed against his mouth, cumming again, but gently, compared to her previous orgasms. She ran the tips of her fingers lightly up and down Dean's back and it made him shiver, and that little additional stimulus was enough. He came as gently as she had, that last time. It wasn't the usual hot rush, but a slow warmth that loosened his whole body, like he was spilling out every bit of tension.

They pulled apart from each other and lay, side by side on the bed. Zakiyyah laid her hand on Dean's arm, as she had done in the bar. Dean tilted his head to look at her. The bedside lamp shone warm gold on her dark, sweaty skin. She smiled up at the ceiling, and her gums were pink, and her teeth were white with a gap at the front.

 

 

* * *

 

 

After that, it became a point of pride for Dean to get a girl to squirt. He loved it, he loved it when it was just a tiny dribble, he loved it when it was a gush that ruined the sheets, but most of all he loved how much the women loved it; even the girls that didn't end up squirting still had a damn good time. Dean had made women kick over bedside lamps, tear holes in sheets and, on one occasion, cum so hard that they got hiccups, all because of what Zakiyyah had shown him.

If Dean were a religious man, he might have thought she was an angel.


End file.
